The purpose of the proposed research to thoroughly understand the basis for chiral recognition between enantiomeric compounds and derivatized or underivatized cyclodextri and then to use this knowledge in a variety of practical and esoteric ways. The interaction of diastereomers and even structural isomers with cyclodextrin based substrates will be considered as well. Three important applications of this work are: the efficient separation of enantiomeric compounds, the determination of absolute configuration by chromatographic means, and the rapid and sensitive determination of optical purity. The importance of this work to the medical and health sciences becomes clear when one realizes that over half of the top 200 prescribed drugs in the United States contain at least one chiral center. Furthermore, it is well known that drug isomers frequently have different physiological properties. A variety of derivatized and underivatized cyclodextrins will be made or isolated and attached to a variety of supports. This will result in a chiral stationary phase that is capable of forming inclusion complexes with several molecules. Interaction energies will be calculated between the cyclodextrins and a variety of chiral model compounds and currently used pharmaceutical compounds. Separation efficiency and resolution of these enantiomeric compounds on different cyclodextrin based packings will be evaluated as well. It is expected that the proposed theoretical and mechanistic work will compliment the more practical analytical and preparative separation methods developed in this study.